I didnt get any feels the first time round playing this game.
I just managed to bang Emi (anal yessssss) and then stay in a relationship with her.
Playing another go, going after Lilly or Hanako. Maybe more feels here.

If earlier on, during the choice in her studio, you demand she explains instead of leaving her alone, she yells "GET OUT" right there, as opposed to in your room later. That breaks you off permanently. It's heavily implied that in that case she really goes "depressed artist mode" later in her life and commits suicide. The creators approved of that theory, she does bite the bullet.